


The Eight-Or-So Men Who Had Enjoyed Seeing Addison Montgomery Naked

by bobbiejelly



Series: Guess Who's Crushing on Addison Montgomery? [17]
Category: Grey's Anatomy, Private Practice
Genre: Crossover, F/F, Femslash, Friendship, MerAdd, meddison
Language: English
Status: In-Progress
Published: 2020-07-16
Updated: 2020-07-16
Packaged: 2021-03-05 05:01:43
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 4,528
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25298800
Author URL: https://archiveofourown.org/users/bobbiejelly/pseuds/bobbiejelly
Summary: And the one woman Addison Montgomery almost wishes who (already) had.
Relationships: Meredith Grey/Addison Montgomery
Series: Guess Who's Crushing on Addison Montgomery? [17]
Series URL: https://archiveofourown.org/series/1797412
Comments: 10
Kudos: 16





	The Eight-Or-So Men Who Had Enjoyed Seeing Addison Montgomery Naked

**Author's Note:**

  * For [LordofLezzies](https://archiveofourown.org/users/LordofLezzies/gifts), [ryleewrites](https://archiveofourown.org/users/ryleewrites/gifts), [LarisUSB](https://archiveofourown.org/users/LarisUSB/gifts), [AddisonAddek](https://archiveofourown.org/users/AddisonAddek/gifts), [Addie_queen](https://archiveofourown.org/users/Addie_queen/gifts).
  * Inspired by [Addison's Anatomy / Meredith's Anatomy](https://archiveofourown.org/works/25238866) by [Addie_queen](https://archiveofourown.org/users/Addie_queen/pseuds/Addie_queen). 



> Little gift for a few people who have been super active in the comments & on social media these days :D.

**Summary for the Chapter:**

> Addison Montgomery (no longer Shepherd) really thought she had her shit together for once.
> 
> Jokes.

_Author's Note:_

To be perfectly upfront here, the heterosexual in this fanfiction is only a light and temporary means to a very homosexual end.

This is inspired by a funny Twitter discussion between LordOfLezzies and I, on the #meddison tag today, which ryleewrites jumped in on as well.

Also, it's set in the pilot of Private Practice, PP-S1-E01, "In which we meet Addison, a nice girl from somewhere else,' hope you enjoy! Spoilers through GA-S3-E25.

_bobbiejelly_

* * *

**The Eight-Or-So Men Who Had Enjoyed Seeing Addison Montgomery Naked**

* * *

_And the one woman Addison Montgomery almost wishes who (already) had._

* * *

**Chapter 1: Open Up My Eager Eyes**

* * *

Addison Montgomery (no longer Shepherd) really thought she had her shit together for once.

_Jokes._

How could she be thinking she had her shit together as she's super-super naked dancing around her new beach house she'd impulsively purchased after her best friend Naomi Bennett had recommended it to her?

Addison hadn't even looked at any alternatives, she'd signed the papers ten times faster than she'd signed her divorce papers to Derek- her ex-husband Dr. Derek Christopher Shepherd, Derek, who'd left her to chase after an admittedly astoundingly gorgeous blonde intern.

Addison sighs.

She really wishes she'd taken more time with her housing selection because she's staring at Naomi Bennett's (ex?) husband straight in the face and he's screaming and she realizes she'd naked- _again._

When Sam Bennett asks her about this, she tells him that at least eight-or-so men have really enjoyed seeing her naked.

He doesn't ask her to count them out, or about why she'd hesitated and then insisted on 'maybe 11,' or something like that.

Come on, she's almost 40 at this point, that's hardly a promiscuous number.

Addison reflects on all of these men who'd enjoyed seeing her without even a skirt or a set of a bra and panties as she tries to settle herself down to start her new work today at the practice.

Today she realizes she doesn't have her shit together nearly at all…

* * *

The first guy who'd seen her naked 'like that,' had been her high school prom date 'Skippy Gold,' who had a head brace like her and who played the oboe.

Addison, herself, had been super into instruments back then and she likes to tell this story to other people now as if she'd been popular back then but she hadn't been.

High school Addison Montgomery had been too-tall but with mini-breasts and had had too many freckles amongst her too-many pimples.

It took forever for her hormones to kick in and get it together to give her some boobies.

And after that, it took forever for her own hormones to settle down enough for her to even talk to a boy 'like that,'.

Addison had known back then that she didn't stand a chance with anyone cooler than her, so she asked out Skippy at the school comic convention and she pretended to Derek later that she'd been bored when he'd talked to her all night about Star Wars but she'd secretly loved it.

Skippy Gold had gotten her naked by calling her 'even more beautiful than Princess Leia.'

She's never told that part of the story to anyone. Ever. (And she never ever ever planned to, either).

* * *

After she'd graduated from her fancy high school or whatever, she headed off to Yale for her undergraduate degree and approximately four-to-ten men had since seen her naked.

Addison doesn't like to admit, either, that she's not so sure about that number.

It's not because she's been with men who've scoffed at her stripped-down figure…

It's that she's half-certain she'd had some drunken encounters where she's woken up naked and so she figured she'd been naked and done stuff with these boys but she can't really be certain.

After all of the drunken-encounters, Addison tries to vow to never drink-and-date again but that seems to last not-so-long so pretty soon she's dating this raven-haired guy named Derek Shepherd.

And he's nice and he's kind and he's oh-so-smart-and-a-future-brain-surgeon and he's got this thing going on where he shows her off to his friends and she thinks that she's falling in love.

She marries him.

She stays with him.

Derek's seen her naked, obviously.

* * *

But then again, so has his best friend Mark Everett Sloan on plenty of occasions though they'd never 'done stuff,' with each other until they'd started having an affair with each other then yeah…

So after that, Mark had been added to the official list of 'people who'd seen Addison Montgomery naked and liked it,' and that's the last person she'd thought she'd ever add to that list until Mark knocks her up and she doesn't keep it and he sleeps around and she doesn't talk to him or Derek for ages.

She's not sure what she's thinking when she shows up to Seattle, but all of a sudden she's introducing herself to Derek's new… (Mistress? Girlfriend? Her name is Meredith Grey?!)... And she's staring her right in the face and she's confused at why all of this is happening.

Derek leaves her eventually via adulterous exam room sex at the prom (which she later finds out about via the missing underwear of the beautiful blonde intern he'd fucked), and Mark takes a transcontinental booty call out to see her again.

When Mark sleeps with her, she doesn't think of him, but she doesn't tell him or Derek or anybody else who she's thinking about (because it's the last person on earth that she really should be thinking about in this way).

The last person who'd seen her naked had been the intern she'd shoved into the on-call room of her former workplace, Seattle Grace Hospital, Alex Karev.

She'd been the one to take all control and he'd been the one to go along with it.

He turned her down after, and she'd turned him down right before leaving.

Addison had said some inspirational things about 'taking chances,' but really she just wanted to let him down easy.

* * *

So all of that comes full-circle now that Sam's seen her naked and Pete Wilder is asking her if she'd moved states just to see him again after he'd kissed her and she's all telling him off about how that's absolutely absurd, even though she's half-certain that Pete doesn't believe her.

"Hey, you moving here, it didn't have anything to do with me kissing you, did it?" asks Pete.

_It doesn't. It really doesn't. But Addison's even more ashamed to admit that part than to admit falsely that it had to do with her kiss with Pete back ages ago in the stairwell._

"What?" says Addison, trying to figure out what Pete just said amongst all of her inner turmoil.

"It's okay, it's just that well… It was just a kiss," says Pete.

_And Addison tries not to flashback to the other 'just a kiss,' that actually made her move across the country in utter desperation._

"You think that I moved here… Just because you kissed me!?" Exclaims Addison in alarm.

_Well, if it had been the truth, or at least it appeared to be, then maybe this wouldn't be so terrible here after all…_

"It was a good kiss. It was an excellent kiss by the-" Pete tries to really over-sell her on this experience Addison had obviously already had because she was there of course, and by now Addison is totally blushing which is making Pete totally overconfident and the whole thing is actually a little bit irritating.

_A part of Addison wishes she could just go back to being satisfied with just kissing Pete._

"Stop talking, alright!?" Says Addison. "I did not move here because you kissed me," Addison huffs in annoyance.

_It's the biggest truth that Addison has spoken all day..._

* * *

They deliver the baby via a surgical procedure and the receptionist and midwifery student, Dell, actually really does help.

Violet saves her patient who was having panic attacks.

Sam and Charlotte King sort out the whole 'sperm-saving,' debacle.

Cooper is great with kids and Pete does his voodoo-magic-y thing.

And in all, it's a decent day and Addison is relaxing later outside their beach houses with her best friend Naomi.

"Why did you really move here?" Naomi asks her out of the blue.

"Huh?" Says Addison, the way she'd said 'huh,' to Pete Wilder earlier.

"I know you didn't move here because of Sam or I, or else you would have the last time. And you didn't move here because of your kiss with Pete because if you had, I know you Addison, and if you wanted that man you'd be off in bed with him by now. So why the hell are you here, Addie? And why do I have to play 'interrogations by Nai,' when you know fine well you're going to spill your guts about this anyway after another glass or so of that red wine," Naomi offers.

Addison sighs, Naomi is right. She'll tell her eventually. Addison always does…

* * *

Naomi talks first though, and shares about a patient of hers whose wife showed up to lay a claim on her now-dead husband-in-name's sperm.

"The wife just walked up to us in the cafeteria and announced that the other girl was a- I can't even say it again," says Naomi.

"Oh God," says Addison.

"What?" Says Naomi, reading something on her best friend's face.

"I did that," says Addison.

"You wanted your dead husband's sperm? Because as far as I know, you don't have one of those anymore and Derek and Mark are both very much still alive," says Naomi.

"No, not that, the other part," says Addison.

"What?" Says Naomi.

"I showed up to Seattle Grace Hospital way back when I fled New York and I introduced myself to Meredith Grey as "Addison Shepherd… And you must be the woman who's been screwing my husband," says Addison with a huff.

"Well, she was, and you were…" Says Naomi.

* * *

"Yeah, but she still doesn't deserve that," says Addison.

"And somehow you're still beating yourself up about this?" Says Naomi.

"I've made a lot of mistakes Nai, but that's one of them. I tried to stick up for her the next day and tell her the truth about how I cheated first and make nice but she didn't want anything to do with me," says Addison.

"And this bothers you because….?" Says Naomi, who is still trying to understand why her best friend is so upset over her ex-husband's ex-mistress.

"It's just not okay, and I'm not okay, it's all not gonna ever be really okay!?" Addison screeches until Naomi comforts her best friend again.

"Whatever it is, Addison, it's going to be okay," says Naomi.

"I really don't think it is," says Addison.

"It feels like that now but it gets better," Naomi promises.

"Okay," says Addison, and she takes a breath and also another sip of red wine.

* * *

"It'll be okay and I'm here for you as your best friend no matter what. Give me some credit! I stuck by you when you cheated on your husband with his best friend and we all had to watch from the sidelines," says Naomi.

Addison flinches, but then she nods.

"Thanks," Addison says weakly.

"You're welcome," says Naomi.

Addison pours herself another glass of wine before starting.

"It wasn't supposed to ever happen like this," Addison begins.

"Of course not," says Naomi before Addison glares at her just a little for interrupting.

_Addison remembers the softest lips ever parting for her to explore._

"I told Pete it would be sort-of deranged for him to think that I would pick up and move because of a kiss but I would and I had and I have and also I rolled my eyes at Dell today because I thought 'midwifery,' wasn't a word and it actually is and he is one. Well, he's going to be a midwife not like, 'a midwifery,' because that's not actually a word and I-" Addison rambles.

_Addison remembers her tongue meeting the sweetest tongue on the planet and sighing._

"It was about a kiss, but not about the one with Pete Wilder," Addison admits finally.

_It was the best kiss she'd ever had. Addison had had Skippy Gold, Derek, Mark, Alex, Pete, and also a few other men she doesn't fully remember. And still, this kiss had been the best out of all of them for her. Ever._

"Okay," says Naomi, motioning for her to go on.

_Addison remembers how she's never wanted that kiss to ever end and how she hated how it had had to. Addison remembers the flush she felt all over her body while being kissed. Addison remembers everything._

* * *

"It was after the wedding," says Addison.

"Wait, which one?" Says Naomi.

"Well, actually, it never ended up being a wedding but that was kind of the point," says Addison.

"Huh?" Says Naomi.

"Uh, Cristina Yang was supposed to marry Preston Burke but he left her at the altar so there wasn't a wedding after all," Addison explains to her best friend.

_There was no wedding and no happy ending for her, then, after her fabulous kiss, either… Addison thinks bitterly._

"Right," Naomi remembers Addison having told her about that bit at some point.

"And anyway, there was some kissing, and a little bit of touching," says Addison vaguely.

_The touching had been even better than just the kissing. The touching over her waist and her hips and her thighs. Addison had been touched by soft hands all over her body but still over her clothes. Addison had had those fine fingers over her figure and she shivered…_

"Are you cold?" Asks Naomi.

"Oh, I guess a little," Addison says idly, as she realizes she's shivering from even just her recollections.

_Addison had been touching back a bit too. Touching. Holding. Caressing…_

"I have no idea how it ended up like this but I just had to get away because I was so freaked out about the kissing because it was just so confusing and I forgot myself and I didn't want to bury myself in someone else that I shouldn't," says Addison.

"I'm going to guess this person wasn't single? Or you weren't?" Says Naomi.

"Actually, technically we were both single, at least at the time by some miracle," Addison shrugs.

_Addison had been relishing the freedom from her wedding ring she had thrown off the ferry-boat and she knew her companion had no outstanding commitments either so she doesn't know why she's left feeling so guilty but she is… Probably because she enjoyed it a bit too much?_

* * *

"So what's the issue if the person was single and you were single, what- was it just a terrible kiss?" Says Naomi.

"Nope," says Addison.

"A good kiss?" Asks Naomi.

"Like you wouldn't believe," Addison sighs nostalgically.

_Addison remembers soft arms cradling her after the kissing, keeping her safe and warm and comforting her. Addison remembers how she hadn't ever felt like this before with Derek or Mark or Pete or Skippy or Alex or anyone and how that scared the crap out of her._

"So why did you run?" Says Naomi.

"I have no idea," Addison deadpans.

 _Addison remembers being asked fervently to stay in Seattle. "Please, Addison," it broke Addison's heart to say no. "Is it because I'm not good enough?" Addison's heart breaks when she hears that part. "No, it's not. It's because_ _I'm_ _not good enough for_ _you_ _," she said._

"Do you think you could go back?" Says Naomi.

"Wouldn't you miss me?" Says Addison.

"Yeah, I'd miss you," says Naomi back to her.

Addison smiles.

" _I'll miss you," Addison was the first one to say that part. "I'll miss you more," Addison is still enveloped in a super-warm body and she closed her eyes and imagined herself staying._

* * *

"You could still go, you know. Get this person back," says Naomi.

"But what about the practice?" Says Addison.

_Addison remembers wishing that that kissing had all been about practicing for more kissing._

"We've been okay for years, we'll be okay again. Besides, we could always hire your brother Archer Montgomery if we're ever that strapped for cash," says Naomi with a chuckle.

"I'm glad I have your blessing either way," says Addison. "You're my best friend- what you think means a lot to me…"

_Addison remembers saying how much the kiss had meant to her._

"Do you think I should call?" Asks Addison weakly.

"Do you want to?" Asks Naomi. (Addison does).

" _You can call, if you want to. You can," Addison considers the words as they're spoken to her. "I probably shouldn't…" Addison hushes. "You only say that now because of the past."_

"Maybe I should call…" Addison muses aloud.

"If you're that hung up still you could always call," says Naomi wisely.

" _I really do like you, Addison. I know it's messed up because of how we met but I really do care about you. And you seem to care about me so why not?" Addison had to turn away then._

* * *

"I think I'll call her," says Addison finally.

"Wait- HER!?" Says Naomi.

"Huh?" Says Addison again, because she's still only half-listening…

" _Is it because I'm a woman and you're a woman?" Addison considers this. "No, I mean, a little. But not entirely. That's not why I'm not staying for you," Addison sighs. "Okay, just checking."_

"I didn't know you were into women," says Naomi.

"To be fair, neither did I until she kissed me," Addison shrugs.

" _Was that the first time you'd kissed a girl ever?" Addison giggled before she said "yeah,'._

"So what, now you're like, a lesbian!?" Says Naomi. "I mean, I'm all cool with you loving who you want and being loved by who you want, I'm just trying to make sure I'm hearing what you are saying," says Naomi empathetically.

"I have no idea, all I know is that I miss kissing her. I've never missed kissing someone like this. Not anyone else and we'd only really kissed once until that point," says Addison.

" _So is this the only time we're going to ever kiss each other?" Addison broke both their hearts when she nodded sadly._

"Do you have feelings for her?" Asks Naomi.

"I tried not having feelings for her but it didn't work," Addison sighs.

" _This feels like more than just kissing," Addison admits to the woman. "I know," she responds. "What, why? How the hell!?" Addison pants. "I have no idea either," she shrugs. "I just love running my hands over your waist," Addison sighs. "I just love holding you," she sighs also._

* * *

"Does she have feelings for you back?" Asks Naomi.

"I think so, but we have just such a history and I'm a bit older and she's just an intern and I don't know, it's Seattle, and I have no idea," Addison says frustratedly.

" _You know, I'll miss you as my teacher, and not just in the kissing-way," Addison is promised by this woman who is still cuddling her. "You were always a good student you know," Addison smiles. She smiles back._

"So if she could very well want you back, what do you have to lose with trying with her?" Asks Naomi.

"Well, I don't know what Derek would say, or Mark or Alex, or even Pete, though I don't talk to Skippy Gold anymore…" Addison shrugs.

"What do your exes have to do with this decision? If you left those people, doesn't that mean you get to move on?" Says Naomi.

" _Is this just about Derek? Like some sort of weird revenge thing? Or like, a sex-bet with Mark?" Addison thinks about it thoughtfully before responding. "No, it's not. And that's much more confusing…"_

"I guess they shouldn't. I guess I shouldn't make up excuses that aren't really real. I guess I should try to do what I want instead of following expectations or trying to make my mother and father and whatnot proud," says Addison.

"Yeah, I mean whatever your family of 'strange Montgomeries,' thinks that's up to them," says Naomi.

" _So then, if it's not about your past or my past… That means you really wanted to kiss ME for me, right?" Addison remembers asking. "Yeah, I just did, at least once," Addison remembers this admission clear as day. "I can't remember someone just wanting me," says Addison, clinging even tighter as her companion held her close to the crook of her neck. "I do," she said. She did._

"Do you think this girl could make you happy?" Asks Naomi.

"Yeah, I just- I'm not sure if I could make her happy and I don't want to hurt her… More… Or ever," says Addison.

* * *

" _He hurt me, when he chose you," Addison hears this confession again as the words echo out into the dark. "I'm sorry," says Addison. "You don't have to be. You had every right to be angry," she says. "I did, but so did you. I took your McDog. I took your McDreamy. I took your Mclife…"_

"What if being together could take some of both of your pain and heartbreak and loneliness away?" Offers Naomi wisely.

"You really think that we could be?" Says Addison.

" _I feel light when I'm with you," even after the pleading about the McThings, Addison can still feel herself being nuzzled into and she loves that. "I'm glad," says Addison. Addison meant it._

"You know what they say about shots people don't take, Addison. Sam and I took our shot, and we're struggling now but we'll get through it. You'll get through this either way, but if you have a shot at finding love again, why would you hold yourself back? Besides, you could be just the person she's waiting for," Naomi offers.

"That's really ironic, that last part, when you say it like that," Addison laughs.

" _Do you think we could ever get past the whole 'the mistress and the wife,' dynamic we sorta have when we're like this?" Addison had been asked rather rhetorically. Addison just shrugged._

* * *

"I think I'll call her, I'll call her now," says Addison.

"I'll give you your privacy," says Naomi with a pat on the back and a wink.

" _Don't you think it's incredibly ironic that we're sneaking off to fool around after a failed wedding?" Said Addison. "You're just worried about bad juju aren't you," she laughs. "A little," she says. "If it helps, we could get hot coach afterward," she laughed. So did Addison._

"Hey," says Addison, once the phone rings a few times and the call finally comes through.

"Hey," says the voice on the other side of the line.

_That's how this thing had all started- the 'hey,' after the wedding after all of the breakups._

"I miss you, I've missed you," Addison gushes.

"I missed you too. I never thought that you'd actually call," she laughs.

_When Addison had had the number given to her she'd cherished it but never dialed it, ever._

* * *

"Do you really want me still? Are you even still single? I mean…?" Addison fumbles.

"Yeah, I still want you, Addison. And I'm single. And I mean it," she smiles into the phone.

_Right before she kissed you, that's what this wonderful woman had said to her. "I want you, Addison," and that had been exactly what Addison wanted and needed to hear._

"I want you, too," Addison confesses.

"All I want is to hold you again," she hears back.

" _Kiss me," Addison had said. And then this woman finally did._

"Will you come back so I can kiss you again?" The woman asks shakily over the phone.

"I think I will," says Addison. "I promise I will," she adds. "I'm on my way back…"

" _Maybe someday you'll make your way back to me…" The woman muses. "Maybe…" Addison breathes heavily, hiding the tears that are forming at the corners of both of her eyes._

"Kiss me again when I land?" This time it's Addison's turn to be a little bit nervous.

"Of course, Addison," she laughs. "I'll pick you up from the airport," she offers.

" _I'd pick you up and wrap my arms around you every night if you'd let yourself keep me," she offers to Addison. It had been tempting; it was very tempting. It had been all that Addison's ever wanted and more…_

* * *

"Meredith Grey?" says Addison finally.

"Yeah?" Says Meredith Grey.

" _Meredith," Addison had panted into the blonde woman's mouth right before she finally let her get back to comfort a distraught Cristina._

"I can't wait to be with you," Addison smiles. "You know, I flew halfway across the damn country because I was afraid of falling in love with you after just one kiss.. But now… I think I'm ready to take that free-fall again with you if you want to," Addison finally articulates.

"You have no idea how worth the wait that you are," says Meredith with her own smile.

" _Do you know how many men have seen me naked?" said Addison to Meredith as they had parted ways. "How many?" Said Meredith. "I have no idea, somewhere between eight and eleven," said Addison. "I bet they all really liked it. I'd really like it," said Meredith._

"Addison?" Asks Meredith.

"Yeah?" Says Addison.

" _Addison," Meredith had sighed into her lips as Addison had kissed the side of her neck up past her jawline. It had been the most sensual and sweet feeling ever._

"Does this mean I get to be the first woman that gets to see you naked like that and like it?" Meredith asks coyly.

"I think it does," says Addison.

" _We have to stop now, we have to stop kissing now because if we keep going like this I'll lose my panties again," Meredith had panted into Addison's mouth. "I'd mail them to you at this point," Addison said with a chuckle. "I'm not ready for this yet with you, but I could be," said Meredith. "Does this mean maybe someday?" Addison had asked hopefully. "Definitely."_

* * *

"Someday finally arrived, today, hey," says Meredith.

"It most certainly did," says Addison.

" _I think I'm falling in love with you," said Meredith Grey. But Addison Montgomery had already walked out the door._

"Addison?" Says Meredith one final time.

"Yeah?" Says Addison.

_Addison Montgomery had actually heard her the first time she'd said that to her from the other side of the door even though she'd pretended she hadn't._

"Meredith?" Says Addison, because she doesn't lie this time.

"Yeah?" Says Meredith, glad to be finally hearing Addison's honesty resurface.

_Addison had pressed her back against the seat and sobbed because she missed the Grey girl the entire time on the flight out of Seattle moving all the way to Los Angeles._

"I think I'm falling in love with you also," Addison finally says into the phone.

"I can't wait until you come home," says Meredith. And it's the truth.

* * *

*

*

*

*

*

***** **END OF CHAPTER 1**

* * *

_Author's Note:_

Song inspiration: Mr. Brightside, by The Killers.

But like, the lesbian version.

Of course… :D.

No idea if this will continue-

Ps. please me know how the format of this story is as a reader!

###  [bobbiejelly](https://archiveofourown.org/users/bobbiejelly/pseuds/bobbiejelly)

**Author's Note:**

> THANKS!


End file.
